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<h1><a href="https://archiveofourown.org/works/22404973">Failed Insights</a> by <a class='authorlink' href='https://archiveofourown.org/users/temporarily_lost_at_sea/pseuds/temporarily_lost_at_sea'>temporarily_lost_at_sea</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Critical Role (Web Series)</td></tr>

<tr><td><b>Genre:</b></td><td>Crack, M/M</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-01-25</td></tr>

<tr><td><b>Updated:</b></td><td>2020-01-25</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-04-28 12:00:08</td></tr>

<tr><td><b>Rating:</b></td><td>General Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>777</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/22404973</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/temporarily_lost_at_sea/pseuds/temporarily_lost_at_sea</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>What if Liam had failed his insight check after Jester told Caleb that Essek said he loved him?<br/>Slight SPOILERS for C2E92</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Essek Thelyss/Caleb Widogast</td></tr>

<tr><td><b>Comments:</b></td><td>8</td></tr>

<tr><td><b>Kudos:</b></td><td>121</td></tr>

</table>

<a name="section0001"><h2>Failed Insights</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>
  <em>“He says he loves you so much, Caleb.” </em>
</p>
<p>
  <em>“Yeah, yeah, insight check, ja.”</em>
</p>
<p>
  <em>Liam’s face fell as he saw the number on his die.</em>
</p>
<p>
  <em>“That’s… a natural one.”</em>
</p>
<p>
  <em>“Alright… Jester, roll a deception check,” Matt said, as the rest of the group burst out laughing.</em>
</p>
<p>
  <em>A roar of laughter erupted from Laura’s side of the table as she stared at he die.</em>
</p>
<p>
  <em>“Natural twenty!!!”</em>
</p>
<p>
  <em>“Okay.” Matt rubbed his temples as he looked at the various states of hilarity among his players. “Caleb, you fully believe that Essek told Jester he loves you.”</em>
</p>
<p>*</p>
<p>“W-what?”</p>
<p>The look on Caleb’s face took Jester by surprise. She’d thought it was obvious she was joking, but he seemed completely taken aback. There was no way he believed what she’d just said, right? Well, there was really only one way to find out...</p>
<p>“Yeah, he said he loves you so, so much and he wants you to come visit him before you leave.” She nodded fervently.</p>
<p>Caleb blinked slowly and got that far away expression he sometimes had when things got too emotional. Watching him carefully, Jester waited for several minutes for him to speak again. The others were moving in and out of the room around them, busy with preparations for the trip.</p>
<p>“But… why would he say such a thing?”</p>
<p>“Gee, I don’t know, Caleb, maybe because he loves you and wants to have lots of sex with you.” She gave him a meaningful look, thinking that he must get the joke now, but instead his face turned a deep shade of crimson.</p>
<p>“Caleb!!!” She shot up from her chair, leaning closer to him in excitement, as the realisation hit her. “Do you like Essek too? Do you want to have lots of sex with Essek?!”</p>
<p>Caleb only shrunk away from her gaze, not making eye contact.</p>
<p>“YOU HAVE TO GO TO HIM CALEB!” She was jumping up and down in excitement now. This was just like in Tusk Love, when Guinevere realised that she had been in love with Oskar all along and she ran to him across the field just as he was leaving! “YOU HAVE TO GO TO HIM AND TELL HIM HOW YOU FEEL!”</p>
<p>“Who does Caleb have to go to?” Nott’s suspicious voice at her elbow almost made Jester jump.</p>
<p>“To Essek of course!” She shouted, as she pushed past the goblin, gripping Caleb by the robes. “To tell him he loves him!!!”</p>
<p>She put her hand in the small of his back and started pushing him towards the door. Even if he had tried to resist he’d been no match to Jester’s bulky arms, but as it were, he just let himself be pushed out onto the doorstep.</p>
<p>“Go to him, Caleb, go to him!” Jester yelled, before slamming the door shut.</p>
<p>Dancing a little victory dance, she stopped as she came face to face with Nott. The goblin was standing with her arms crossed, eyening Jester suspiciously.</p>
<p>“What’s going on?”</p>
<p>“Ohmygosh, Nott, it’s so amazing!” She gripped Notts arms and started dancing around with her. “When I sent a message to Essek to tell him we were leaving he said “okay and tell Caleb I love him and I want to see him before you leave ‘cause I want to have sex with him one time in case you all die” and now Caleb is going to him to tell him-”</p>
<p>“Did he really say that?” Nott asked, trying to hold Jester still.</p>
<p>“YES-” Jester halted, letting her thoughts catch up with her. Oh, he hadn’t really said that, had he? “Well, no he didn’t actually…” She giggled. “I was just joking, but then Caleb took it seriously and it looked like he really wanted it to be true, so I thought I’d help him a bit.”</p>
<p>Nott sighed.</p>
<p>“That’s nice, but you know you can’t push him like that. Caleb is a sensitive boy, he can’t handle it.”</p>
<p>At the same time Beau opened the front door, coming back from some last minute provisioning.</p>
<p>“Er, why is Caleb out there, looking like he just fried someone?”</p>
<p>“Oh no, he’s still here?” Disgruntled, Jester walked up to the window. “He’s supposed to go to Essek and have sex!”</p>
<p>“O-kay…” Beu looked from Jester to Nott, who gave her a small shake of the head. “I’ll… just...go pack this.” She waved her bag of supplies vaguely and fled to the next room.</p>
<p>Nott joined Jester at the window to look at Caleb, who was standing motionless just outside the door, dull eyes staring blindly in front of him.</p>
<p>“We’d better get him.”</p>
<p>“Okay,” Jester conceded. “But I’m definitely going to message Essek again tonight.”</p>
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